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Full text of "Nicotine insecticides. Part VII, Search for synergists (continued)"

STATE 



ROARD 
March 1952 E-836 

United States Department of Agriculture 

Agricultural Research Administration 

Bureau of Entomology and Plant Quarantine 



NICOTINE INSECTICIDES. Part VII--SEARCH FOR SYNERGISTS (Continued) 

By E. L. Mayer, Carl Robertson, and R. H. Nelson, Division of Stored 
Product Insect Investigations/^ Bureau of Entomology and Plant Quar- 
antine, and C. F. Woodward, Eastern Regional Research Laboratory, 
Bureau of Agricultural and Industrial Chemistry 



The search for compounds to replace some of the nicotine in insecti- 
cides and thus make its use more economical has been continued. This 
paper reports results with IOC chemicals that were tested similarly to 
those discussed in Parts II and V of this series (E-709 and E-768). The 
materials were furnished by the Eastern Regional Research Laboratory 
of the Bureau of Agricultural and Industrial Chemistry and were tested 
at the Anaheim, Calif., laboratory of the Bureau of Entomology and Plant 
Quarantine. 

Material and Methods 

A dust containing 2 percent of nicotine sulfate and 5 percent of adjunct 
was compared with a 5-percent nicotine sulfate standard for leaf-feeding 
larvae or a 3.5-percent standard for the pea aphid. The mortality caused 
by some mixtures was compared with that induced by the two components 
when used separately. The comparisons were made at approximately the 
same deposit. All mixtures were diluted with attapulgite. 

Some of the materials were chosen at random, but most of them were 
selected because of close chemical resemblance to phthalonitrile and 
bis(p_-chlorophenyl) sulfide, the two best materials discussed in E-768. 

The test insects included third instars of the armyworm ( Pseudaletia 
unipuncta (Haw.)) and the diamondback moth (Plutella maculipennis (Curt.)), 
fourth instars of the green dock beetle ( Gastrophysa cyanea Melsh.), and 
the second nymphal stage of the pea aphid ( Macrosiphum pisi (Kltb.)). 

All the larvae were fed dusted foliage in 9 -cm. petri dishes, whereas 
the aphids were dusted directly on the plants on which they were feeding 
and then confined in battery jars 16.5 cm. in diameter and covered with 



1/ Formerly the Division of Control Investigations. 



-2 - 



cloth caps. In preliminary fumigation tests the insects were placed in 
the lower half of a petri dish, a filter paper 11 cm. in diameter dusted 
with the toxicant was placed over the dish, and the top half put in place. 
This makes a rather close fitting fumigation chamber and, in addition, 
keeps the insects from coming into contact with the insecticide. For all 
tests the deposits ranged from 75 to 200 micrograms per square centi- 
meter. Approximately 35 larvae and 40 or more aphids were used in 
each test. Each material was tested against 3 or 4 species. Mortality 
counts of the larvae were made after 3 days and those of the aphids 
after 1 day. 

Phytotoxicity tests with the materials showing the most promise 
were made on plants of bean, beet, broccoli, celery, collard, eggplant, 
lettuce, pepper, swiss chard, and tomato. 

Discussion of Results 

A material was considered to be a possible synergist for nicotine 
if the mortality caused by a mixture of the two (table 1, column A) was 
approximately the same or above that caused by the nicotine standard 
(B). If synergism was indicated in tests against two or more species 
of insects, the material was later subjected to developmental testing. 
The materials in table 1 were selected on this basis and their evaluations 
can be found in the A-B column. This table also presents mortalities 
caused by dusts containing 2 percent of nicotine as the sulfate (C) and in 
some cases 5 percent of adjunct (D) when used alone. Column A-(C + D) 
shows the difference between the kill produced by the mixture and the 
additive kills of nicotine and adjunct when tested separately. 

On the basis of the averages of mortalities of all tests the materials 
in table 1 compared favorably with the 5 -percent standard, except tall 
oil nitrile (Arneel TOD), bis(p-bromophenyl) sulfide, and bis(p-chloro- 
phenyl) disulfide. Of the materials on which a preliminary determination 
could be made for the presence of synergism (A-(C + D)), alpha-naphtho- 
nitrile and methyleneaminoacetonitrile were good. A single test with 
bis(p-chlorophenyl) disulfide against the pea aphid did not show promise. 

Alpha -naphthonitrile is a volatile material and in a fumigation test 
a 5-percent dust of it killed 64 percent of the armyworms. Fluorene 
when mixed with nicotine sulfate was as effective as the standards against 
the armyworm and the pea aphid, but no further tests were made, since 
its continued use is dangerous to the investigator. 

Phytotoxicity tests showed that against five varieties of plants 
methyleneaminoacetonitrile, tall oil nitrile, and bis(p-chlorophenyl) 
disulfide v/ere not injurious at 1 -percent concentrations. Phenyl 
sulfoxide, m-nitrobenzonitrile, and monochlorodibenzothiophene caused 
considerable burning, while 2-chlorodibenzothiophene and Aroclor 1232 
caused moderate injury. Tests were not made on the other adjuncts 
given in table 1. 



-3- 

Adjuncts in mixtures with nicotine that showed synergism against one 
insect only are shown in table 2. 

From the data presented six adjuncts were chosen for quantitative 
testing- -isophthalonitrile, methyleneaminoacetonitrile, alpha- naphtho- 
nitrile, tall oil nitrile, bis(p-bromophenyl) sulfide, and bis(p-chlorophenyl) 
disulfide. 

The following adjuncts in mixtures with nicotine showed no synergism 
against the armyworm, the diamondback moth, and the pea aphid: 



Acenaphthene 

Adiponitrile 

m-Aminobenzonitrile 

gamma -Aminoisobutyric acid 

Anthracene 

Benzonitrile 

Benzothiazole, 2-mercapto- 

Benzoylacetonitrile 

di-n-Butylcyanamide 

n-Capronitrile 

Calcium gluconate 

Carbazole 

Chloracetonitrile 

p-Chlorobenzonitrile 

beta -Chloropropionitrile 

Cyanoacetamide 

Dibenzothiophene, 2,8-dichloro- 

Diethyl fumarate 

l,l-Dimethyl-2-acetylethylene 

oxide 
Dimethyl fumarate 
5, 5 -Dim ethylhydantoin 
Dimethyl maleate 
Ditolyl sulfide 
2-Ethyl-l-hexanol 
Ethyl beta-phenyl-alpha- 

cyanoacrylate 
Furfuryl alcohol 
Glycolonitrile 

3 -Hydroxy- 3 -methyl - 2 -butanone 
Iso-capronitrile 
Isophorone 

beta-Isopropoxypropionitrile 
Itaconic acid 
Metaldehyde 
1 -Methylnaphthalene 



2 -Methylnaphthalene 

1 -Methyl-2-propene-l -ol 

1 -Methyl-2^propene-l -ol-acetate 

Myrcene 

beta-Naphthoylacetonitrile 

Paraldehyde 

Phenol, 2,2-methylenebis (4-chloro- 

Phenol, 2,2-methylenebis [4,6- 

dichloro- 
gamma - Phenoxybutyronitr ile 
Phenylacetonitrile 
beta -Phenypropionitr ile 
Phenyl sulfide, 4-hydroxy- 
Phenyl sulfide, 4-hydroxy-4'- 

methyl 
Phenyl sulfide, 4-methoxy-4'- 

methyl 
Phenyl sulfone, 5,5'-dichloro-2-2'- 

dihydroxy 
Phenyl sulfone, 4 methoxy- 
Propionitrile 

Red oil nitrile (Arneel ROD) 
Stearonitrile (Arneel 18D) 
Succinonitrile 
Tetrahydrofurfuryl acetate 
Tetrahydrofurfuryl alcohol 
Thianthrene, 2,6-dichloro- 
m-Tolunitrile 
o-Tolunitrile 
p-Tolunitrile 
alpha, alpha, beta-Trichloro- 

propionitrile 
s-Trioxane 
n-Valeronitrile 
Veratr aldehyde 
p-Xenyl sulfide 



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UNIVERSITY OF FLORIDA 



-8 



3 1262 09239 6356 



Table 2. --Adjuncts in mixture with nicotine showing synergism against 
one insect only 



Adjunct 



Armyworm 



Diamondback 
moth 



Pea aphid 



Acrylonitrile 

n-Butyronitrile 

delta -Chlorovaleronitrile 

Coco nitrile (Arneel CD) 

Cyanamid 

Cyanoacetanilide 

alpha- Cyanoethyl acetate 

Cyanuric acid 

Decane nitrile (Arneel 10D) 

Dicapryl tetrahydrophthalate 

Diethyl phthalate 

Ethoxypropionitrile 

Lactonitrile 

Lauryl cyanide 

alpha -Naphthaleneacetonitrile 

p-Nitrobenzonitrile 

p-Nitrophenylacetonitrile 

Phthalamide 

Pivalonitrile 

Tetradecane nitrile (Arneel 14D) 

Thianthrene 

Tribromophenyl sulfide 

Triethyl phosphate 



x 
x 



x 



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X 

X 
X 
X 
X 
X 
X 
X 

X 
X 



X 
X